The Sydney Charles Experience

Meet Sydney


photo by Joe Mazza

“Charles… is remarkably well cast in director Kenneth L. Roberson’s production. She doesn’t, as would some, have Ronnie Scott’s veneer to shake off. On the contrary. She is naturally intimidating and goes right to where Simone would have been in that moment.  “

- Chris Jones on ‘Nina Simone: Four Women’


“Sydney Charles is an incredible talent… She projects an incredible vocal range and delivers every song with perfection. “

- PerformInk on ‘The Wiz’


“Charles almost stole the show with her portrayal of Tillie. She was amazingly funny with her spot on performance . “

- Chicago Now on ‘Guess Who’s Coming to Dinner’



photo by Joel Maisonet



Sydney Charles is an award-winning actress hailing from Chicago, IL who committed her life to acting after years as a banker and operations coordinator and she is deeply grateful for the opportunity.

Selected theatre credits include: The Color Purple (Drury Lane Theatre), Lottery Day (Goodman Theatre), Nina Simone: Four Women (Northlight Theatre), Flyin' West (American Blues Theatre), Father Comes Home From the Wars (Goodman Theatre), Guess Who's Coming to Dinner (Court Theatre), Insurrection: Holding History (Stage Left Theatre - original run and Theatre on the Lake), four editions of The Fly Honey Show (The Inconvenience), Spamilton Chicago (Royal George Theatre), An Octoroon (Definition Theatre Company), Dorothy in The Wiz (Kokandy Productions), Zora in the world premiere of Prowess (Jackalope Theatre), and the title role in Dessa Rose (Bailiwick Chicago).

Her directing debut was with Wildclaw Theatre with their yearly Deathscribe Festival of Horror Plays, and she has served as Associate Director for the World Premiere of His Shadow at 16th Street Theatre and The Shipment at Red Tape Theatre.

Sydney can also be seen in episodes of The Haven (web series), The T(web series), and Shameless (Showtime). Recently, Sydney has also begun to do voice-over work for McDonald’s and Xfinity Comcast. She is also particularly proud to be an artistic associate with Firebrand Theater--the recently formed feminist musical theater company.

Sydney thanks God for every opportunity she is given and her circle for supporting her every step of the way. Represented by Stewart Talent.

 “There’s nothing like performing. It’s not about the attention for me; it’s about being fulfilled. “


photo by Matthew Gregory Hollis




The Color Purple - ‘Shug Avery’

Drury lane theatre / lili-anne brown

Lottery Day - ‘Zora’

Goodman Theatre / Lili-Anne Brown

Nina Simone: Four Women - ‘Nina Simone’

Northlight Theatre / Kenneth Roberson

Flyin’ West - ‘Fannie Dove’

American Blues Theatre / Chuck Smith

Father Comes Home From The Wars (Parts 1, 2,& 3) - ‘Second’

Goodman Theatre / Niegel Smith

Guess Who’s Coming to Dinner - ‘Matilda “Tillie” Binks’

Court Theatre / Marti Lyons

Insurrection: Holding History - ‘Mistress Mo’tel’/’Gertha’

Stage Left Theatre / Wardell Julius Clark

A Swell in the Ground - ‘Olivia’

The Gift Theatre Company / Chika Ike

Lottery Day - ‘Zora’

Goodman Theatre / Lili-Anne Brown

An Octoroon - ‘Minnie’

Definition Theatre Company / Chuck Smith

Spamilton - ‘Renee’

Royal George / Gerard Alessandrini

The Wiz - ‘Dorothy’

Kokandy Productions / Lili-Anne Brown

The Snowy Day - ‘Mom’/Female Player

Emerald City Theatre / Jacqueline Stone

Octagon - ‘The Watcher Named Pen’

Jackalope Theatre / Tara Branham

The Fly Honey Show - Company Member

The Inconvenience / Erin Kilmurray

Prowess - ‘Zora’

Jackalope Theatre / Marti Lyons

Myths and Hymns - Woman 2

BoHo Ensemble Theater / Peter Robel

Ragtime - ‘Sarah’

Big Noise Theater / Stacey Flaster

Dessa Rose - ‘Dessa Rose’

Bailiwick Chicago / Lili-Anne Brown

Mr. Chickee’s Funny Money - ‘Lynetta’ (US)

Chicago Children’s Theater / Derrick Sanders

The Color Purple - ‘Darlene/Ensemble’

Mercury Theater / Walter Stearns

Smokey Joe’s Café - ‘Brenda’

Theo-Ubique Cabaret Theater / Brenda Didier

Cats - ‘Grizabella’

Theo-Ubique Cabaret Theater / Brenda Didier



The Devil Wears Prada - ‘Ms. Mills/Ensemble’

Broadway nyc / anna shapiro

Greetings From Moscow - ‘Masha Chekova’

Timeline Theatre Company / Elly Green

Jackson State Kent State - ‘Myrtle Green’

Timeline Theatre Company / Wardell Julius Clark

Purlie Victorious - ‘Lutiebelle’

Broadway NYC / Anna Shapiro

Wade - ‘Frankie’

Goodman Theatre / Marti Lyons

Florissant and Canfield - ‘Rubix’

Goodman Theatre / Monty Cole

Girls in Cars Underwater. - ‘Bree’

Victory Gardens / Will Davis



The Right Swipe - ‘Chynna’

OpenTV/Independent/ Justin Casselle

The T - ‘Becca’

OpenTV/Independent/ Bea Cordelia Sullivan-Knoff

Shameless - ‘Grace ‘

Showtime / Emmy Rossum

Did It Before - ‘Sydney’

Independent / Mamadou Sewa Bah

The Haven - ‘Fae’

Independent / Layne Marie Williams

Empire - Featured Vocalist

FOX / Debbie Allen



Academy Sports & Outdoors - ‘Mom’

One at Optimus / Tim Mason



McDonald’s - Radio Commerical

Burrell Communications

McDonald’s - Radio Commercial

Burrell Communications

Xfinity Comcast - Radio Commercial

Burrell Communications

Bruh Rabbit - Podcast

Make Believe Association

PleasureTown - Podcast

WBEZ Radio

Mercury Theatre - Radio Commercial

Clear Channel Communications



His Shadow - Associate Director

16th Street Theatre / Wardell julius clark

The Shipment - Associate Director

Red Tape Theare / Wardell Julius Clark

Loaners - Director

Wildclaw Theatre

The Wiz - ‘Assistant Director’

Chicago State University / Wendell Tucker



Best Supporting Performer - Guess Who’s Coming to Dinner

Joseph Jefferson Award Nomination

2018 Players 50 Theater/Music/Dance/Comedy

NewCity Stage  

Leading Performance in a Musical – The Wiz

Time Out Chicago Theater Award Recipient

Best Actress in a Musical – The Wiz

Black Theatre Alliance Award

Best Actor in a Musical – The Wiz

The Hawk Chicago Award Recipient 

Best Actress in a Musical – The Wiz

Joseph Jefferson Award Nomination